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Acta Cryst. (2007). E63, m2364    [ doi:10.1107/S1600536807036835 ]

Bis(4,4'-di-tert-butyl-2,2'-bipyridine-[kappa]2N,N')silver(I) trifluoromethanesulfonate

T. Fischer, M. Zabel, H. Yersin and U. Monkowius

Abstract top

In the crystal structure of the title compound, [Ag(C18H24N2)2](CF3SO3), the Ag atoms are coordinated by four N atoms of two 4,4'-di-tert-butyl-2,2'-bipyridine (tert-bubpy) ligands within a strongly distorted tetrahedron.

Comment top

Crystals of the title compound were obtained as a side-product in the preparation of [(tert.-bubpy)2Pt]CF3O3S in acetonitrile solution. To identify this compound a single-crystal structure analysis was performed.

The asymmetric unit consists of one complex cation [(tert.-bubpy)2Ag]+ and one [CF3O3S]− anion, which are located in general positions. The Ag atom is coordinated by four nitrogen atoms of two tert.-bubpy ligands within a strongly distorted tetrahedron. The four Ag—N bonds are similar and are in the range of 2.305 (3)–2.333 (3) Å. The bite angles are 72.66 (9) and 72.16 (10) ° [(N1—Ag1—N2) and (N3—Ag1—N4), respectively]. These values are typical for bpy ligands in Ag(I) complexes (Bowmaker et al., 2005). The tert.-bubpy ligands deviate from planarity significantly [(N1—C5—C6—N2) −21.5 (6) and (N3—C23—C24—N4) −25.2 (4) °].

Related literature top

For related literature, see: Bowmaker et al. (2005).

Experimental top

The title complex was isolated as a side-product in the preparation of [(tert.-bubpy)2Pt]CF3O3S. For the synthesis of this Pt complex via [Pt(NCMe)4]CF3O3S, K2PtCl4 and Ag(CF3O3S) were suspended in acetonitrile. After 2 h of stirring the reaction mixture was filtrated to remove the precipitating AgCl and the solvent was distilled off in vacuum. Without further purification the obtained white powder was stirred with an excess of 4,4'-di-tert.-butyl-2,2'-bipyridine in CH2Cl2 at r.t. The Pt complex was precipitated with hexanes and isolated by filtration. Obviously, the precursor complex [Pt(NCMe)4]CF3O3S contained considerable amounts of a silver species, because the title complex [(tert.-bubpy)2Ag]CF3O3S was obtained as yellow crystals after cooling of the filtrated solution in the refrigerator.

Refinement top

All hydrogen atoms were positioned with idealized geometry and refined isotropic using a riding model with C—H = 0.96 Å] for methyl and C—H = 0.93 for aromatic H atoms. Uiso(H) values were set to 1.2 Ueq (1.5 Ueq for methyl) of the parent atom. Some of the carbon atoms of the tert-butyl groups shows unusual large anisotropic displacement parameters indicative for disordering. However, a refinement uisng a split model does not lead to a significant improvement of the structure model.

Computing details top

Data collection: IPDS (Stoe & Cie, 1998); cell refinement: IPDS; data reduction: X-RED (Stoe & Cie, 1998); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

Figures top
[Figure 1] Fig. 1. View of the title compound with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level.
Bis(4,4'-di-tert-butyl-2,2'-bipyridine-κ2N,N')silver(I) trifluoromethanesulfonate top
Crystal data top
[Ag(C18H24N2)2](CF3SO3)Z = 2
Mr = 793.73F000 = 824
Triclinic, P1Cell parameters were determined by indexing 8000 reflections with I/sigma limit 6.0.
Hall symbol: -P 1Dx = 1.360 Mg m−3
a = 9.9251 (17) ÅMo Kα radiation
λ = 0.71073 Å
b = 13.3620 (18) ÅCell parameters from 8000 reflections
c = 15.9435 (19) Åθ = 2.2–27.0º
α = 78.435 (15)ºµ = 0.63 mm−1
β = 84.990 (17)ºT = 295 K
γ = 69.339 (18)ºPrism, yellow
V = 1937.9 (5) Å30.23 × 0.17 × 0.12 mm
Data collection top
Stoe IPDS
diffractometer		7777 independent reflections
Radiation source: fine-focus sealed tube5433 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.037
T = 295(1) Kθmax = 27.0º
φ scansθmin = 2.2º
Absorption correction: analytical
[from crystal shape; X-SHAPE and X-RED (Stoe & Cie, 1998)]		h = −12→12
Tmin = 0.859, Tmax = 0.915k = −16→17
22997 measured reflectionsl = −20→20
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047H-atom parameters constrained
wR(F2) = 0.140  w = 1/[σ2(Fo2) + (0.0861P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
7777 reflectionsΔρmax = 0.77 e Å−3
442 parametersΔρmin = −0.50 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
[Ag(C18H24N2)2](CF3SO3)γ = 69.339 (18)º
Mr = 793.73V = 1937.9 (5) Å3
Triclinic, P1Z = 2
a = 9.9251 (17) ÅMo Kα
b = 13.3620 (18) ŵ = 0.63 mm−1
c = 15.9435 (19) ÅT = 295 K
α = 78.435 (15)º0.23 × 0.17 × 0.12 mm
β = 84.990 (17)º
Data collection top
Stoe IPDS
diffractometer		7777 independent reflections
Absorption correction: analytical
[from crystal shape; X-SHAPE and X-RED (Stoe & Cie, 1998)]		5433 reflections with I > 2σ(I)
Tmin = 0.859, Tmax = 0.915Rint = 0.037
22997 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.047442 parameters
wR(F2) = 0.140H-atom parameters constrained
S = 1.04Δρmax = 0.77 e Å−3
7777 reflectionsΔρmin = −0.50 e Å−3
Special details top

Experimental. Data were collected applying an imaging plate system (Stoe) with the following measurement parameters:

Detector distance [mm] 65 Phi movement mode Oscillation Phi incr. [degrees] 1.4 Number of exposures 194 Irradiation / exposure [min] 3.00

For a detailed description of the method see: Sheldrick, G·M., Paulus, E. Vertesy, L. & Hahn, F. (1995) Acta Cryst. B51, 89–98.

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ag10.76501 (4)0.05607 (2)0.25906 (1)0.0653 (1)
N10.7378 (3)0.1950 (2)0.14261 (15)0.0508 (9)
N20.8067 (4)−0.0206 (2)0.13780 (16)0.0554 (9)
N30.8393 (3)0.0903 (2)0.38163 (15)0.0503 (9)
N40.6759 (3)−0.0370 (2)0.37763 (15)0.0493 (8)
C10.7275 (4)0.2978 (3)0.1460 (2)0.0567 (10)
C20.7424 (4)0.3718 (3)0.0764 (2)0.0537 (10)
C30.7691 (4)0.3430 (3)−0.00515 (19)0.0466 (10)
C40.7826 (4)0.2363 (3)−0.00852 (18)0.0484 (10)
C50.7654 (4)0.1651 (3)0.06562 (18)0.0480 (10)
C60.7767 (4)0.0513 (3)0.06272 (18)0.0485 (10)
C70.7522 (4)0.0222 (3)−0.01157 (19)0.0532 (10)
C80.7550 (4)−0.0834 (3)−0.0123 (2)0.0524 (10)
C90.7855 (5)−0.1557 (3)0.0657 (2)0.0639 (13)
C100.8102 (5)−0.1226 (3)0.1369 (2)0.0652 (13)
C110.7785 (4)0.4266 (3)−0.0848 (2)0.0534 (10)
C120.8981 (6)0.4703 (4)−0.0732 (3)0.0809 (17)
C130.6352 (5)0.5197 (3)−0.0945 (3)0.0747 (14)
C140.8108 (6)0.3776 (3)−0.1666 (2)0.0751 (16)
C150.7265 (5)−0.1165 (3)−0.0936 (2)0.0625 (13)
C160.6101 (7)−0.0220 (4)−0.1481 (3)0.097 (2)
C170.8640 (7)−0.1465 (10)−0.1432 (5)0.187 (5)
C180.6651 (11)−0.2095 (6)−0.0730 (4)0.141 (4)
C190.8914 (4)0.1709 (3)0.3809 (2)0.0595 (13)
C200.8901 (4)0.2158 (3)0.4514 (2)0.0583 (11)
C210.8338 (4)0.1783 (3)0.5295 (2)0.0496 (10)
C220.7794 (4)0.0951 (3)0.53029 (18)0.0467 (10)
C230.7828 (4)0.0531 (2)0.45618 (18)0.0441 (9)
C240.7211 (4)−0.0339 (2)0.45442 (17)0.0435 (9)
C250.7160 (4)−0.1101 (3)0.52774 (19)0.0481 (10)
C260.6656 (4)−0.1954 (3)0.5235 (2)0.0499 (10)
C270.6206 (4)−0.1966 (3)0.4431 (2)0.0576 (13)
C280.6267 (4)−0.1178 (3)0.3738 (2)0.0580 (11)
C290.8231 (4)0.2319 (3)0.6082 (2)0.0563 (11)
C300.6958 (7)0.3397 (4)0.5946 (4)0.0938 (19)
C310.9582 (6)0.2577 (7)0.6161 (4)0.117 (3)
C320.7945 (10)0.1617 (5)0.6897 (3)0.117 (3)
C330.6695 (5)−0.2856 (3)0.6013 (2)0.0576 (13)
C340.6815 (18)−0.2528 (7)0.6824 (3)0.260 (10)
C350.7979 (7)−0.3834 (5)0.5897 (5)0.146 (3)
C360.5380 (8)−0.3174 (7)0.6059 (5)0.155 (3)
S10.64907 (16)0.61423 (11)0.22335 (9)0.0869 (5)
F10.8850 (6)0.5950 (6)0.2871 (5)0.206 (4)
F20.7421 (8)0.5286 (5)0.3770 (2)0.187 (3)
F30.8608 (6)0.4380 (4)0.2800 (4)0.165 (2)
O10.5899 (6)0.7159 (3)0.2491 (3)0.130 (2)
O20.7180 (5)0.6117 (3)0.1412 (2)0.1054 (16)
O30.5594 (6)0.5447 (5)0.2418 (4)0.153 (3)
C370.7952 (8)0.5385 (5)0.2913 (5)0.110 (3)
H10.709000.319400.199000.0680*
H20.735000.441200.082900.0650*
H40.803300.21230−0.060600.0580*
H70.733500.07360−0.061900.0640*
H90.78890−0.226900.069300.0770*
H100.83060−0.173200.187700.0780*
H12A0.988300.41120−0.065200.0970*
H12B0.876100.50480−0.023900.0970*
H12C0.904700.52230−0.123100.0970*
H13A0.615400.55270−0.044500.0900*
H13B0.560000.49240−0.101100.0900*
H13C0.639500.57300−0.144000.0900*
H14A0.735600.35120−0.175100.0900*
H14B0.901200.31860−0.161300.0900*
H14C0.815700.43250−0.214800.0900*
H16A0.641700.03950−0.164000.1160*
H16B0.52190−0.00210−0.115400.1160*
H16C0.59450−0.04470−0.198800.1160*
H17A0.93540−0.20590−0.109400.2250*
H17B0.89600−0.08520−0.157700.2250*
H17C0.84950−0.16800−0.194800.2250*
H18A0.57570−0.18660−0.041800.1690*
H18B0.73240−0.27170−0.038900.1690*
H18C0.64900−0.22830−0.125300.1690*
H190.930300.197600.329900.0710*
H200.927200.271700.446900.0700*
H220.740400.067000.580800.0560*
H250.74600−0.104600.579700.0580*
H270.58640−0.250800.436300.0690*
H280.59500−0.120600.321400.0700*
H30A0.609100.325600.588600.1130*
H30B0.712900.386200.543700.1130*
H30C0.685800.374600.643000.1130*
H31A0.971300.306300.565500.1410*
H31B1.040000.191600.622800.1410*
H31C0.948700.291500.665100.1410*
H32A0.871100.092500.698100.1410*
H32B0.704900.150900.685400.1410*
H32C0.789300.197000.737300.1410*
H34A0.60050−0.189100.689300.3120*
H34B0.76890−0.237100.681600.3120*
H34C0.68280−0.310800.729300.3120*
H35A0.88350−0.364700.585000.1740*
H35B0.78760−0.407400.538500.1740*
H35C0.80470−0.440600.638100.1740*
H36A0.53330−0.344000.555000.1860*
H36B0.45360−0.255100.610600.1860*
H36C0.54300−0.373400.655000.1860*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ag10.1025 (3)0.0651 (2)0.0316 (1)−0.0345 (2)−0.0021 (1)−0.0052 (1)
N10.0720 (19)0.0471 (14)0.0333 (11)−0.0201 (14)−0.0024 (11)−0.0075 (10)
N20.079 (2)0.0468 (14)0.0367 (12)−0.0172 (15)−0.0057 (12)−0.0053 (11)
N30.0677 (18)0.0551 (15)0.0345 (11)−0.0292 (14)0.0002 (11)−0.0082 (11)
N40.0688 (18)0.0510 (14)0.0355 (11)−0.0292 (14)−0.0078 (11)−0.0056 (10)
C10.079 (2)0.0523 (18)0.0397 (14)−0.0190 (18)−0.0018 (15)−0.0164 (13)
C20.071 (2)0.0441 (16)0.0492 (16)−0.0202 (16)−0.0056 (15)−0.0129 (13)
C30.0539 (19)0.0461 (16)0.0437 (14)−0.0212 (15)−0.0031 (13)−0.0083 (12)
C40.064 (2)0.0479 (16)0.0364 (13)−0.0232 (16)0.0006 (13)−0.0083 (12)
C50.064 (2)0.0450 (16)0.0360 (13)−0.0198 (15)−0.0046 (13)−0.0063 (12)
C60.064 (2)0.0446 (16)0.0359 (13)−0.0184 (15)−0.0013 (13)−0.0053 (12)
C70.081 (2)0.0444 (16)0.0364 (13)−0.0256 (17)−0.0045 (14)−0.0035 (12)
C80.067 (2)0.0462 (17)0.0436 (15)−0.0178 (16)0.0000 (14)−0.0111 (13)
C90.098 (3)0.0434 (17)0.0512 (17)−0.0259 (19)−0.0042 (18)−0.0063 (14)
C100.101 (3)0.0447 (18)0.0438 (16)−0.0198 (19)−0.0081 (17)−0.0014 (13)
C110.068 (2)0.0503 (17)0.0464 (15)−0.0275 (17)−0.0020 (15)−0.0053 (13)
C120.088 (3)0.084 (3)0.088 (3)−0.051 (3)0.005 (2)−0.018 (2)
C130.083 (3)0.062 (2)0.068 (2)−0.019 (2)−0.002 (2)0.0026 (19)
C140.114 (4)0.066 (2)0.0462 (17)−0.037 (2)0.010 (2)−0.0057 (16)
C150.086 (3)0.060 (2)0.0479 (17)−0.027 (2)−0.0063 (17)−0.0183 (15)
C160.126 (5)0.084 (3)0.082 (3)−0.027 (3)−0.037 (3)−0.017 (3)
C170.089 (4)0.353 (14)0.132 (6)−0.021 (6)0.004 (4)−0.175 (8)
C180.263 (10)0.113 (5)0.095 (4)−0.120 (6)−0.056 (5)−0.002 (3)
C190.077 (3)0.067 (2)0.0447 (16)−0.041 (2)0.0076 (15)−0.0070 (15)
C200.074 (2)0.060 (2)0.0538 (17)−0.0390 (19)0.0023 (16)−0.0115 (15)
C210.059 (2)0.0460 (16)0.0469 (15)−0.0203 (15)0.0021 (14)−0.0123 (13)
C220.060 (2)0.0460 (16)0.0376 (13)−0.0230 (15)0.0014 (13)−0.0076 (12)
C230.0551 (19)0.0420 (15)0.0373 (13)−0.0197 (14)−0.0021 (12)−0.0062 (11)
C240.0572 (19)0.0436 (15)0.0335 (12)−0.0215 (14)−0.0017 (12)−0.0075 (11)
C250.064 (2)0.0471 (16)0.0381 (14)−0.0242 (16)−0.0034 (13)−0.0082 (12)
C260.063 (2)0.0437 (16)0.0452 (15)−0.0222 (16)0.0002 (14)−0.0062 (13)
C270.078 (3)0.0555 (19)0.0538 (17)−0.0393 (19)−0.0068 (16)−0.0099 (15)
C280.076 (2)0.066 (2)0.0432 (15)−0.036 (2)−0.0133 (15)−0.0086 (15)
C290.065 (2)0.059 (2)0.0559 (17)−0.0278 (18)0.0021 (16)−0.0249 (16)
C300.104 (4)0.087 (3)0.095 (3)−0.021 (3)−0.003 (3)−0.048 (3)
C310.089 (4)0.199 (7)0.108 (4)−0.070 (5)0.022 (3)−0.100 (5)
C320.235 (8)0.098 (4)0.044 (2)−0.084 (5)0.000 (3)−0.022 (2)
C330.080 (3)0.0487 (18)0.0501 (16)−0.0335 (19)−0.0091 (16)0.0019 (14)
C340.67 (3)0.161 (7)0.039 (2)−0.268 (12)−0.014 (6)0.013 (3)
C350.108 (5)0.109 (5)0.158 (6)−0.012 (4)0.002 (4)0.066 (5)
C360.117 (5)0.165 (7)0.164 (6)−0.087 (5)−0.033 (4)0.098 (6)
S10.0946 (9)0.0808 (8)0.0881 (8)−0.0286 (7)0.0153 (6)−0.0319 (6)
F10.151 (4)0.265 (7)0.264 (7)−0.123 (5)−0.029 (4)−0.082 (6)
F20.312 (8)0.180 (5)0.069 (2)−0.088 (5)−0.026 (3)−0.004 (2)
F30.181 (5)0.102 (3)0.180 (4)−0.009 (3)−0.045 (4)−0.011 (3)
O10.142 (4)0.088 (3)0.151 (4)−0.012 (3)0.013 (3)−0.061 (3)
O20.161 (4)0.087 (2)0.0691 (19)−0.045 (2)0.016 (2)−0.0198 (17)
O30.132 (4)0.207 (6)0.191 (5)−0.124 (4)0.035 (4)−0.091 (5)
C370.128 (5)0.085 (4)0.122 (5)−0.049 (4)−0.010 (4)−0.003 (3)
Geometric parameters (Å, °) top
Ag1—N12.306 (2)C33—C351.499 (8)
Ag1—N22.305 (3)C33—C361.501 (10)
Ag1—N32.328 (3)C1—H10.9300
Ag1—N42.333 (3)C2—H20.9300
S1—C371.761 (8)C4—H40.9300
S1—O31.473 (7)C7—H70.9300
S1—O11.406 (4)C9—H90.9300
S1—O21.425 (4)C10—H100.9300
F1—C371.347 (10)C12—H12C0.9600
F2—C371.419 (9)C12—H12A0.9600
F3—C371.311 (8)C12—H12B0.9600
N1—C51.342 (4)C13—H13A0.9600
N1—C11.353 (5)C13—H13B0.9600
N2—C61.358 (4)C13—H13C0.9600
N2—C101.354 (5)C14—H14A0.9600
N3—C191.347 (5)C14—H14B0.9600
N3—C231.348 (4)C14—H14C0.9600
N4—C241.353 (4)C16—H16A0.9600
N4—C281.346 (5)C16—H16B0.9600
C1—C21.366 (5)C16—H16C0.9600
C2—C31.406 (5)C17—H17A0.9600
C3—C41.396 (5)C17—H17B0.9600
C3—C111.534 (5)C17—H17C0.9600
C4—C51.400 (5)C18—H18C0.9600
C5—C61.495 (5)C18—H18B0.9600
C6—C71.384 (5)C18—H18A0.9600
C7—C81.404 (5)C19—H190.9300
C8—C151.529 (5)C20—H200.9300
C8—C91.396 (5)C22—H220.9300
C9—C101.368 (5)C25—H250.9300
C11—C121.535 (7)C27—H270.9300
C11—C131.519 (6)C28—H280.9300
C11—C141.534 (5)C30—H30A0.9600
C15—C161.546 (7)C30—H30B0.9600
C15—C171.484 (10)C30—H30C0.9600
C15—C181.536 (10)C31—H31C0.9600
C19—C201.373 (5)C31—H31A0.9600
C20—C211.393 (5)C31—H31B0.9600
C21—C221.394 (6)C32—H32C0.9600
C21—C291.543 (5)C32—H32A0.9600
C22—C231.399 (4)C32—H32B0.9600
C23—C241.499 (5)C34—H34B0.9600
C24—C251.398 (4)C34—H34A0.9600
C25—C261.412 (6)C34—H34C0.9600
C26—C331.539 (5)C35—H35A0.9600
C26—C271.399 (5)C35—H35B0.9600
C27—C281.378 (5)C35—H35C0.9600
C29—C301.535 (7)C36—H36A0.9600
C29—C311.519 (8)C36—H36B0.9600
C29—C321.511 (7)C36—H36C0.9600
C33—C341.473 (8)
Ag1···H17Bi3.7200H13B···H14A2.4900
Ag1···H31Bii3.4400H13C···H12C2.5100
Ag1···H32Aii3.5000H13C···H14C2.4600
Ag1···H34Aiii3.5400H13C···H34Cix2.4000
Ag1···H36Biii3.6700H14A···H42.2800
F1···O12.852 (9)H14A···H13B2.4900
F1···O22.900 (8)H14A···H32Cx2.5900
F2···O12.920 (7)H14A···C42.7800
F2···O32.864 (9)H14B···H12A2.5200
F3···O22.909 (7)H14B···C42.8000
F3···O32.883 (9)H14B···H42.3100
F1···H31Civ2.8400H14C···H13C2.4600
O1···C28v3.390 (6)H14C···H12C2.4600
O1···F22.920 (7)H14C···H35Cix2.5900
O1···F12.852 (9)H16A···C72.6900
O2···F32.909 (7)H16A···H72.1300
O2···C9v3.374 (6)H16A···H17B2.4800
O2···F12.900 (8)H16B···H18A2.4000
O3···F22.864 (9)H16B···C73.0800
O3···F32.883 (9)H16C···H17C2.4800
O1···H28v2.6800H16C···H18C2.3900
O2···H22.5800H17A···H18B2.5600
O2···H9v2.5300H17B···C72.9700
O3···H13Bvi2.8300H17B···Ag1i3.7200
N1···C62.415 (4)H17B···H16A2.4800
N1···N22.732 (4)H17C···H16C2.4800
N2···N12.732 (4)H17C···H18C2.5000
N2···C52.423 (4)H18A···H16B2.4000
N3···N42.745 (4)H18A···C92.9900
N3···C242.417 (4)H18B···H92.1100
N4···N32.745 (4)H18B···H17A2.5600
N4···C232.425 (4)H18B···C92.6900
N4···H31Bii2.8500H18C···H16C2.3900
C2···C13vi3.518 (7)H18C···H17C2.5000
C9···O2vii3.374 (6)H20···C312.7000
C12···C12viii3.588 (8)H20···H35Aii2.5600
C13···C2vi3.518 (7)H20···H31A2.1500
C28···O1vii3.390 (6)H22···C252.7600
C2···H13A2.7500H22···C322.5400
C2···H12B2.7600H22···H32B2.1300
C2···H13Bvi2.9500H22···H32A2.5100
C4···H14A2.7800H22···H252.2800
C4···H14B2.8000H25···C342.5300
C4···H72.6900H25···C222.7500
C7···H16A2.6900H25···H34B2.1100
C7···H16B3.0800H25···H222.2800
C7···H42.7100H25···H34A2.5200
C7···H17B2.9700H27···H30Aiii2.5700
C9···H18A2.9900H27···C362.7300
C9···H18B2.6900H27···H36A2.1800
C12···H12Bviii2.9800H28···O1vii2.6800
C12···H22.8800H30A···H32B2.4500
C13···H22.9400H30A···H27iii2.5700
C14···H42.5200H30B···C202.9200
C16···H72.6700H30B···H31A2.4300
C18···H92.6000H30C···H31C2.4700
C20···H31A2.6900H30C···H32C2.4600
C20···H30B2.9200H31A···C202.6900
C22···H252.7500H31A···H30B2.4300
C22···H32A2.8900H31A···H202.1500
C22···H32B2.6900H31B···Ag1ii3.4400
C23···H36Biii2.9600H31B···N4ii2.8500
C24···H31Bii2.9300H31B···C24ii2.9300
C25···H34B2.6600H31B···H32A2.5700
C25···H34A2.8800H31C···H30C2.4700
C25···H222.7600H31C···H32C2.4400
C27···H36A2.7100H31C···F1iv2.8400
C27···H35B2.9000H32A···H222.5100
C31···H202.7000H32A···H31B2.5700
C32···H222.5400H32A···Ag1ii3.5000
C34···H252.5300H32A···C222.8900
C36···H272.7300H32B···H30A2.4500
H2···H13A2.3900H32B···C222.6900
H2···C132.9400H32B···H222.1300
H2···H12B2.3300H32C···H30C2.4600
H2···O22.5800H32C···H14Axi2.5900
H2···C122.8800H32C···H31C2.4400
H4···C142.5200H34A···C252.8800
H4···H72.2000H34A···H252.5200
H4···H14A2.2800H34A···H36B2.4800
H4···H14B2.3100H34A···Ag1iii3.5400
H4···C72.7100H34B···H252.1100
H7···C162.6700H34B···C252.6600
H7···H42.2000H34B···H35A2.4400
H7···C42.6900H34C···H13Cxii2.4000
H7···H16A2.1300H34C···H35C2.4100
H9···C182.6000H34C···H36C2.3500
H9···H18B2.1100H35A···H20ii2.5600
H9···O2vii2.5300H35A···H34B2.4400
H12A···H14B2.5200H35B···C272.9000
H12B···C22.7600H35B···H36A2.3700
H12B···H22.3300H35C···H34C2.4100
H12B···H12Bviii2.5900H35C···H36C2.4400
H12B···C12viii2.9800H35C···H14Cxii2.5900
H12B···H13A2.4700H36A···C272.7100
H12C···H14C2.4600H36A···H272.1800
H12C···H13C2.5100H36A···H35B2.3700
H13A···H12B2.4700H36B···H34A2.4800
H13A···H22.3900H36B···C23iii2.9600
H13A···C22.7500H36B···Ag1iii3.6700
H13B···O3vi2.8300H36C···H34C2.3500
H13B···C2vi2.9500H36C···H35C2.4400
N1—Ag1—N272.66 (9)C10—C9—H9120.00
N1—Ag1—N3113.58 (9)N2—C10—H10118.00
N1—Ag1—N4152.56 (11)C9—C10—H10118.00
N2—Ag1—N3152.82 (12)H12B—C12—H12C109.00
N2—Ag1—N4115.29 (10)C11—C12—H12A110.00
N3—Ag1—N472.16 (10)C11—C12—H12B109.00
O3—S1—C37101.1 (4)C11—C12—H12C110.00
O1—S1—O3115.6 (4)H12A—C12—H12B109.00
O1—S1—C37105.7 (3)H12A—C12—H12C110.00
O1—S1—O2117.3 (3)H13B—C13—H13C110.00
O2—S1—C37101.4 (3)C11—C13—H13C110.00
O2—S1—O3112.9 (3)C11—C13—H13A109.00
C1—N1—C5117.1 (3)C11—C13—H13B110.00
Ag1—N1—C5116.0 (2)H13A—C13—H13B109.00
Ag1—N1—C1125.3 (2)H13A—C13—H13C109.00
C6—N2—C10116.7 (3)C11—C14—H14B110.00
Ag1—N2—C6115.3 (2)C11—C14—H14A110.00
Ag1—N2—C10124.1 (2)H14A—C14—H14C109.00
C19—N3—C23117.2 (3)C11—C14—H14C109.00
Ag1—N3—C19123.3 (2)H14A—C14—H14B110.00
Ag1—N3—C23115.6 (2)H14B—C14—H14C109.00
Ag1—N4—C24115.2 (2)C15—C16—H16C109.00
Ag1—N4—C28123.7 (2)C15—C16—H16A109.00
C24—N4—C28117.4 (3)C15—C16—H16B110.00
N1—C1—C2124.1 (3)H16B—C16—H16C109.00
C1—C2—C3120.0 (3)H16A—C16—H16B109.00
C2—C3—C11120.8 (3)H16A—C16—H16C109.00
C4—C3—C11123.1 (3)H17A—C17—H17B110.00
C2—C3—C4116.1 (3)H17A—C17—H17C109.00
C3—C4—C5120.7 (3)H17B—C17—H17C109.00
N1—C5—C4122.1 (3)C15—C17—H17C109.00
N1—C5—C6116.6 (3)C15—C17—H17A109.00
C4—C5—C6121.3 (3)C15—C17—H17B110.00
N2—C6—C5116.2 (3)C15—C18—H18A109.00
N2—C6—C7122.0 (3)H18A—C18—H18B109.00
C5—C6—C7121.7 (3)C15—C18—H18B109.00
C6—C7—C8121.2 (3)C15—C18—H18C109.00
C7—C8—C9115.7 (3)H18A—C18—H18C109.00
C9—C8—C15122.5 (3)H18B—C18—H18C110.00
C7—C8—C15121.9 (3)C20—C19—H19118.00
C8—C9—C10120.5 (4)N3—C19—H19118.00
N2—C10—C9123.8 (3)C21—C20—H20120.00
C3—C11—C14112.2 (3)C19—C20—H20120.00
C12—C11—C13109.4 (4)C21—C22—H22120.00
C3—C11—C12109.3 (3)C23—C22—H22119.00
C3—C11—C13108.5 (3)C26—C25—H25120.00
C12—C11—C14108.8 (4)C24—C25—H25120.00
C13—C11—C14108.7 (3)C28—C27—H27120.00
C16—C15—C18104.7 (5)C26—C27—H27120.00
C8—C15—C16111.1 (3)N4—C28—H28118.00
C8—C15—C17107.5 (5)C27—C28—H28118.00
C8—C15—C18111.7 (3)H30A—C30—H30C109.00
C16—C15—C17109.8 (5)C29—C30—H30A109.00
C17—C15—C18112.0 (6)C29—C30—H30B109.00
N3—C19—C20123.6 (3)C29—C30—H30C109.00
C19—C20—C21120.5 (4)H30A—C30—H30B109.00
C20—C21—C29121.4 (3)H30B—C30—H30C110.00
C22—C21—C29122.5 (3)H31A—C31—H31C109.00
C20—C21—C22116.0 (3)C29—C31—H31B109.00
C21—C22—C23120.9 (3)H31B—C31—H31C109.00
C22—C23—C24122.1 (3)C29—C31—H31A110.00
N3—C23—C22121.8 (3)C29—C31—H31C109.00
N3—C23—C24116.1 (2)H31A—C31—H31B110.00
N4—C24—C23116.4 (2)C29—C32—H32B109.00
N4—C24—C25122.1 (3)C29—C32—H32A109.00
C23—C24—C25121.5 (3)H32A—C32—H32C110.00
C24—C25—C26120.5 (3)C29—C32—H32C109.00
C27—C26—C33122.1 (3)H32A—C32—H32B109.00
C25—C26—C27115.9 (3)H32B—C32—H32C109.00
C25—C26—C33121.8 (3)C33—C34—H34C110.00
C26—C27—C28120.4 (4)C33—C34—H34A109.00
N4—C28—C27123.7 (3)C33—C34—H34B110.00
C31—C29—C32110.5 (5)H34A—C34—H34C109.00
C21—C29—C31111.0 (4)H34B—C34—H34C109.00
C21—C29—C30107.6 (3)H34A—C34—H34B109.00
C30—C29—C32108.1 (5)H35A—C35—H35B109.00
C21—C29—C32111.6 (4)H35A—C35—H35C110.00
C30—C29—C31107.9 (5)C33—C35—H35A109.00
C26—C33—C34112.0 (5)C33—C35—H35B109.00
C34—C33—C35109.3 (7)C33—C35—H35C109.00
C26—C33—C35107.5 (4)H35B—C35—H35C110.00
C26—C33—C36111.3 (4)H36B—C36—H36C109.00
C34—C33—C36108.9 (8)C33—C36—H36A109.00
C35—C33—C36107.7 (5)C33—C36—H36B109.00
C2—C1—H1118.00C33—C36—H36C110.00
N1—C1—H1118.00H36A—C36—H36B110.00
C1—C2—H2120.00H36A—C36—H36C109.00
C3—C2—H2120.00S1—C37—F1109.2 (5)
C3—C4—H4120.00S1—C37—F2108.4 (6)
C5—C4—H4120.00S1—C37—F3114.9 (6)
C6—C7—H7119.00F1—C37—F2106.0 (7)
C8—C7—H7119.00F1—C37—F3113.3 (7)
C8—C9—H9120.00F2—C37—F3104.6 (6)
N2—Ag1—N1—C1−168.3 (3)C1—C2—C3—C4−1.7 (6)
N3—Ag1—N1—C1−16.6 (3)C2—C3—C11—C13−60.9 (5)
N4—Ag1—N1—C180.0 (4)C11—C3—C4—C5−176.5 (4)
N2—Ag1—N1—C5−3.3 (3)C2—C3—C4—C52.0 (6)
N3—Ag1—N1—C5148.4 (3)C2—C3—C11—C1258.3 (5)
N4—Ag1—N1—C5−115.0 (3)C4—C3—C11—C12−123.3 (4)
N1—Ag1—N2—C6−8.3 (3)C4—C3—C11—C13117.5 (4)
N3—Ag1—N2—C6−116.3 (3)C2—C3—C11—C14179.0 (4)
N4—Ag1—N2—C6143.4 (3)C4—C3—C11—C14−2.5 (6)
N1—Ag1—N2—C10−165.3 (4)C3—C4—C5—C6178.8 (4)
N3—Ag1—N2—C1086.7 (5)C3—C4—C5—N1−1.1 (6)
N4—Ag1—N2—C10−13.6 (4)N1—C5—C6—C7156.0 (4)
N1—Ag1—N3—C19−13.7 (3)C4—C5—C6—C7−23.9 (6)
N2—Ag1—N3—C1984.3 (3)C4—C5—C6—N2158.6 (4)
N4—Ag1—N3—C19−164.9 (3)N1—C5—C6—N2−21.5 (6)
N1—Ag1—N3—C23143.7 (2)C5—C6—C7—C8−176.3 (4)
N2—Ag1—N3—C23−118.4 (3)N2—C6—C7—C81.1 (6)
N4—Ag1—N3—C23−7.6 (2)C6—C7—C8—C15179.3 (4)
N1—Ag1—N4—C24−113.0 (3)C6—C7—C8—C9−0.8 (6)
N2—Ag1—N4—C24145.8 (2)C7—C8—C9—C100.1 (7)
N3—Ag1—N4—C24−6.0 (2)C7—C8—C15—C16−36.3 (6)
N1—Ag1—N4—C2889.5 (3)C15—C8—C9—C10−179.9 (4)
N2—Ag1—N4—C28−11.7 (3)C9—C8—C15—C17−96.1 (6)
N3—Ag1—N4—C28−163.5 (3)C9—C8—C15—C16143.7 (5)
O2—S1—C37—F168.0 (6)C7—C8—C15—C1783.9 (6)
O3—S1—C37—F1−175.7 (6)C7—C8—C15—C18−152.8 (5)
O1—S1—C37—F260.1 (6)C9—C8—C15—C1827.2 (7)
O2—S1—C37—F2−177.0 (5)C8—C9—C10—N20.3 (8)
O3—S1—C37—F2−60.7 (5)N3—C19—C20—C210.4 (6)
O1—S1—C37—F3176.7 (6)C19—C20—C21—C22−0.6 (6)
O1—S1—C37—F1−54.8 (6)C19—C20—C21—C29−176.4 (4)
O3—S1—C37—F355.9 (7)C20—C21—C29—C3075.8 (5)
O2—S1—C37—F3−60.4 (6)C22—C21—C29—C3218.7 (6)
C5—N1—C1—C20.5 (6)C29—C21—C22—C23175.9 (4)
Ag1—N1—C5—C613.6 (5)C22—C21—C29—C31142.4 (5)
Ag1—N1—C1—C2165.3 (3)C22—C21—C29—C30−99.8 (5)
Ag1—N1—C5—C4−166.5 (3)C20—C21—C29—C31−42.0 (6)
C1—N1—C5—C6179.9 (4)C20—C21—C22—C230.1 (6)
C1—N1—C5—C4−0.2 (6)C20—C21—C29—C32−165.8 (5)
C6—N2—C10—C90.0 (7)C21—C22—C23—C24−178.1 (3)
C10—N2—C6—C5176.9 (4)C21—C22—C23—N30.5 (6)
Ag1—N2—C10—C9156.7 (4)C22—C23—C24—C25−28.9 (5)
C10—N2—C6—C7−0.6 (6)N3—C23—C24—N4−25.2 (4)
Ag1—N2—C6—C518.1 (5)C22—C23—C24—N4153.5 (3)
Ag1—N2—C6—C7−159.4 (3)N3—C23—C24—C25152.4 (3)
Ag1—N3—C19—C20157.2 (3)C23—C24—C25—C26−176.1 (3)
Ag1—N3—C23—C2419.2 (4)N4—C24—C25—C261.4 (6)
C19—N3—C23—C24178.0 (3)C24—C25—C26—C27−0.9 (6)
C19—N3—C23—C22−0.7 (5)C24—C25—C26—C33175.2 (4)
C23—N3—C19—C200.3 (6)C25—C26—C27—C280.0 (6)
Ag1—N3—C23—C22−159.5 (3)C27—C26—C33—C34−164.4 (8)
Ag1—N4—C24—C25−159.8 (3)C27—C26—C33—C3575.5 (6)
C28—N4—C24—C23176.8 (3)C27—C26—C33—C36−42.2 (6)
C28—N4—C24—C25−0.8 (5)C25—C26—C33—C35−100.4 (5)
Ag1—N4—C24—C2317.8 (4)C33—C26—C27—C28−176.1 (4)
C24—N4—C28—C27−0.2 (6)C25—C26—C33—C3419.8 (9)
Ag1—N4—C28—C27156.9 (3)C25—C26—C33—C36141.9 (5)
N1—C1—C2—C30.5 (7)C26—C27—C28—N40.6 (6)
C1—C2—C3—C11176.9 (4)
Symmetry codes: (i) −x+2, −y, −z; (ii) −x+2, −y, −z+1; (iii) −x+1, −y, −z+1; (iv) −x+2, −y+1, −z+1; (v) x, y+1, z; (vi) −x+1, −y+1, −z; (vii) x, y−1, z; (viii) −x+2, −y+1, −z; (ix) x, y+1, z−1; (x) x, y, z−1; (xi) x, y, z+1; (xii) x, y−1, z+1.
Table 1
Selected geometric parameters (Å, °) top
Ag1—N12.306 (2)Ag1—N32.328 (3)
Ag1—N22.305 (3)Ag1—N42.333 (3)
N1—Ag1—N272.66 (9)N2—Ag1—N3152.82 (12)
N1—Ag1—N3113.58 (9)N2—Ag1—N4115.29 (10)
N1—Ag1—N4152.56 (11)N3—Ag1—N472.16 (10)
N1—C5—C6—N2−21.5 (6)N3—C23—C24—N4−25.2 (4)
Acknowledgements top

This work was supported by the Bundesministerium für Bildung und Forschung (BMBF).

references
References top

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119.

Bowmaker, G. A., Effendy, initials?, Marfuah, S., Skelton, B. W. & White, A. H. (2005). Inorg. Chim. Acta, 358, 4371–4388 and references therein.

Sheldrick, G. M. (1997). SHELXL97. University of Göttingen, Germany.

Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13.

Stoe & Cie (1998). X-RED (Version 1.11), X-SHAPE (Version 1.03) and IPDS (Version 2.89). Stoe & Cie, Darmstadt, Germany.